JP6752196B2 - ビスイミドジカルボン酸の製造方法 - Google Patents
ビスイミドジカルボン酸の製造方法 Download PDFInfo
- Publication number
- JP6752196B2 JP6752196B2 JP2017511026A JP2017511026A JP6752196B2 JP 6752196 B2 JP6752196 B2 JP 6752196B2 JP 2017511026 A JP2017511026 A JP 2017511026A JP 2017511026 A JP2017511026 A JP 2017511026A JP 6752196 B2 JP6752196 B2 JP 6752196B2
- Authority
- JP
- Japan
- Prior art keywords
- melting point
- point component
- diamine
- component
- dicarboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 238000002844 melting Methods 0.000 claims description 97
- 230000008018 melting Effects 0.000 claims description 97
- 239000000203 mixture Substances 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 18
- 150000004985 diamines Chemical class 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 16
- -1 aromatic tricarboxylic acid Chemical class 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 150000004984 aromatic diamines Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 claims 3
- 238000003756 stirring Methods 0.000 description 20
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 16
- 150000003628 tricarboxylic acids Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000004566 IR spectroscopy Methods 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000004949 mass spectrometry Methods 0.000 description 6
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 5
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WTNDADANUZETTI-UHFFFAOYSA-N cyclohexane-1,2,4-tricarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1 WTNDADANUZETTI-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- FWHUTKPMCKSUCV-UHFFFAOYSA-N 1,3-dioxo-3a,4,5,6,7,7a-hexahydro-2-benzofuran-5-carboxylic acid Chemical compound C1C(C(=O)O)CCC2C(=O)OC(=O)C12 FWHUTKPMCKSUCV-UHFFFAOYSA-N 0.000 description 2
- YLFZBPFYWIFYCP-UHFFFAOYSA-N 4-(4-carboxyphenyl)phthalic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 YLFZBPFYWIFYCP-UHFFFAOYSA-N 0.000 description 2
- 239000004962 Polyamide-imide Substances 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002612 dispersion medium Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BTHGHFBUGBTINV-UHFFFAOYSA-N naphthalene-2,3,6-tricarboxylic acid Chemical compound C1=C(C(O)=O)C(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 BTHGHFBUGBTINV-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229920003055 poly(ester-imide) Polymers 0.000 description 2
- 229920002312 polyamide-imide Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- BIYNCFPBGDWKOG-UHFFFAOYSA-N 3h-naphthalene-2,2-diamine Chemical compound C1=CC=CC2=CC(N)(N)CC=C21 BIYNCFPBGDWKOG-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- OIFQXZBVIMTLEF-UHFFFAOYSA-N anthracene-2,3,6-tricarboxylic acid Chemical compound C1=C(C(O)=O)C(C(O)=O)=CC2=CC3=CC(C(=O)O)=CC=C3C=C21 OIFQXZBVIMTLEF-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- CBLAIDIBZHTGLV-UHFFFAOYSA-N dodecane-2,11-diamine Chemical compound CC(N)CCCCCCCCC(C)N CBLAIDIBZHTGLV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- PWSKHLMYTZNYKO-UHFFFAOYSA-N heptane-1,7-diamine Chemical compound NCCCCCCCN PWSKHLMYTZNYKO-UHFFFAOYSA-N 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000010152 pollination Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/0013—Controlling the temperature of the process
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/06—Formation or introduction of functional groups containing nitrogen of amide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/16—Polyester-imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015078792 | 2015-04-07 | ||
JP2015078792 | 2015-04-07 | ||
PCT/JP2016/061291 WO2016163412A1 (ja) | 2015-04-07 | 2016-04-06 | ビスイミドジカルボン酸の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2016163412A1 JPWO2016163412A1 (ja) | 2018-02-01 |
JP6752196B2 true JP6752196B2 (ja) | 2020-09-09 |
Family
ID=57073097
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017511026A Active JP6752196B2 (ja) | 2015-04-07 | 2016-04-06 | ビスイミドジカルボン酸の製造方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10501415B2 (zh) |
EP (1) | EP3281938B1 (zh) |
JP (1) | JP6752196B2 (zh) |
KR (1) | KR20170132752A (zh) |
CN (1) | CN107531626B (zh) |
TW (1) | TWI698427B (zh) |
WO (1) | WO2016163412A1 (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EA033834B1 (ru) | 2014-07-31 | 2019-11-29 | Exelixis Inc | Способ получения кабозантиниба, меченного фтором-18, и его аналогов |
JP7232521B2 (ja) * | 2018-07-05 | 2023-03-03 | ユニチカ株式会社 | ポリアミドイミド樹脂の製造方法 |
EP3819283A4 (en) * | 2018-07-05 | 2022-03-16 | Unitika Ltd. | METHOD OF MAKING AN ORGANIC COMPOUND |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1116379A (en) * | 1964-07-09 | 1968-06-06 | Eastman Kodak Co | Copolyimides |
JPS4419274B1 (zh) | 1965-03-30 | 1969-08-21 | ||
JPS494077B1 (zh) | 1970-12-28 | 1974-01-30 | ||
JPS5033120A (zh) | 1973-07-27 | 1975-03-31 | ||
US4066631A (en) | 1975-05-19 | 1978-01-03 | Pennwalt Corporation | Process for preparation of linear polyamide-imides from aromatic tricarboxylic acid anhydrides and diamines |
FR2399452A1 (fr) | 1977-08-05 | 1979-03-02 | France Etat | Polyamide-imide a base d'adamantane et procede pour sa fabrication |
JPS55120628A (en) | 1979-03-13 | 1980-09-17 | Sumitomo Chem Co Ltd | Production of aromatic polyamide-imide polymer |
US4291149A (en) | 1980-01-16 | 1981-09-22 | Standard Oil Company (Indiana) | Injection moldable amide imide copolymers and terpolymers |
JPH078912B2 (ja) | 1985-08-13 | 1995-02-01 | 三井石油化学工業株式会社 | ポリアミドイミド |
JPS63117035A (ja) | 1986-11-05 | 1988-05-21 | Toray Ind Inc | 熱可塑性ポリエ−テルイミドアミド |
US4861862A (en) | 1987-12-31 | 1989-08-29 | General Electric Company | Polyetherimide amide from polyoxyalkylene diimide dicarboxylic acid |
BE1008499A3 (nl) | 1994-07-11 | 1996-05-07 | Dsm Nv | Polyamide-imide. |
JPH0859614A (ja) | 1994-08-23 | 1996-03-05 | Mitsubishi Gas Chem Co Inc | ビスジカルボキシミド類の製造方法 |
US5939520A (en) | 1997-09-05 | 1999-08-17 | Air Products And Chemicals, Inc. | Gas separation membranes based on regiospecific polyamide-imides |
JP2001122858A (ja) | 1999-10-22 | 2001-05-08 | Kawasaki Kasei Chem Ltd | フタルイミド化合物の製造方法 |
JP4822257B2 (ja) | 2005-10-28 | 2011-11-24 | 独立行政法人産業技術総合研究所 | 芳香族カルボン酸イミドの製造方法 |
WO2011121850A1 (ja) | 2010-03-29 | 2011-10-06 | 日立化成工業株式会社 | ナジイミド骨格を有するポリアミドイミド及びその製造方法 |
-
2016
- 2016-04-06 KR KR1020177027003A patent/KR20170132752A/ko unknown
- 2016-04-06 US US15/564,667 patent/US10501415B2/en active Active
- 2016-04-06 CN CN201680019999.1A patent/CN107531626B/zh active Active
- 2016-04-06 WO PCT/JP2016/061291 patent/WO2016163412A1/ja active Application Filing
- 2016-04-06 EP EP16776578.3A patent/EP3281938B1/en active Active
- 2016-04-06 TW TW105110738A patent/TWI698427B/zh active
- 2016-04-06 JP JP2017511026A patent/JP6752196B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
TW201700456A (zh) | 2017-01-01 |
KR20170132752A (ko) | 2017-12-04 |
EP3281938A1 (en) | 2018-02-14 |
CN107531626B (zh) | 2020-08-11 |
WO2016163412A1 (ja) | 2016-10-13 |
JPWO2016163412A1 (ja) | 2018-02-01 |
US20180086704A1 (en) | 2018-03-29 |
TWI698427B (zh) | 2020-07-11 |
US10501415B2 (en) | 2019-12-10 |
EP3281938A4 (en) | 2018-02-14 |
EP3281938B1 (en) | 2019-09-18 |
CN107531626A (zh) | 2018-01-02 |
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